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The Power of Stupidity: How I Dumbed My Way Out of Failure

The worst moment in my life was when I thought I was at the peak of my intelligence.

I honestly thought I was the smartest person on the planet.

I had built and sold a company that year, something I had never done before. I had started another one that was going to eventually raise $100 million. And in the prior few years I had finally achieved the rank of “master” in chess tournaments.

I was a GENIUS!

If you can make it here, you can make it anywhere! I was so high on myself I’d walk in the middle of the street and cars would swerve to avoid me.

I bought a house. I bought art. I flew helicopters rather than drive a few miles.

I invested in companies. I played poker every night and quickly got good enough to play against the professionals of that time.

And changing diapers is a lot more complicated than people think. You have to clean out every speck of S***T down there. They didn’t teach what was down there in Biology 101.

And if you go on vacation with babies your only job is to keep them alive.

And the beach is gross. It’s like lying on dirt and rocks while you try to read a book. Oh, and you have to keep your babies from dying.

But I’ve gone off on a tangent.

PLUS, MINUS, EQUAL — OR….HOW I FOUND OUT HOW STUPID I WAS

I’ve been playing ping pong for 40 years. I had a table in my basement. All my friends had tables. We’d play all day.

I thought I was good. I’ve played maybe 10,000 games. And I love the game.

A few weeks ago I decided to take my own advice. I wanted to get better at this game I loved. So I needed to find my “PLUS, MINUS, EQUAL“.

PLUS — someone to teach me and mentor me.EQUAL — people to play and challenge me so I can put my new learnings to use.MINUS — someone to teach so I can really try to understand at a nuanced level, the things I was learning.

“Your follow through is wrong. You’re responding to my slams wrong. You’re serving wrong. You have no control. Your holding your backhand all wrong so you become unstable on every hit and lose balance.”

He went on and on. He listed 20 more things I was doing wrong over the next hour.

I went back the next day. 20 more things I was doing wrong. I was inconsistent. I couldn’t switch from forehand to backhand.

I didn’t know when to play slow and fast. And my wrist! And my stroke! Over and over!

“Close the racket!” he kept yelling. “Shit,” I said and tried to do what he said and then I forgot again. “Close the racket! Close the racket!”

He said, “I’ve played every sport: boxing, tennis, football, basketball, ping pong. Ping pong is the hardest sport. Because so many things to remember.”

And I was forgetting them over and over.

“Good!” he would yell once every twenty shots. “Again!” right back at me he fired a ball.

I hit it over his head. “Close the racket! Close the racket! Stand more sideways! Move your finger down! Short strokes!”

“Shit.” I couldn’t help myself from saying that. “Why can’t I remember?”

He limped around the table. He adjust everything. He called someone over. The 9 time champion of Africa.

“Hit it to me,” he told the guy. “Loosen your arm,” he said and I did and the other champ hit the ball to us and he moved my arm to hit the ball back 20 times in a row. Returning slam after slam and slamming back.

“See! Do it like that,” he said. “Thanks,” he said to the guy who said, “Always for you”, and then he limped back to his side and started hitting it to me. I missed the first shot.

“Close the racket!” he said.

“Shit,” I said.

I wanted to limp also. Within a week I really looked up to him. We’d spend the down time with me asking questions about his life.

He had story after story. “Wait,” I said, “Let’s save this for the podcast. Then I’ll get the whole story.”

Which I will. I have so much to learn. Not about ping pong. About survival. About getting through things.

I’ve been through so much already. Sometimes I’m tired of going through it again.

In business, in relationships, in career, in friendships, in learning how to judge people. In not being afraid to be judged.

But I have so much to learn from people who have their own stories. I want to absorb all the stories.

MY PLUS-es are not about ping pong. They are about me. I want to be James+.

“When I was 13 I owned 5 guns and had a baby…” he told me. And the stories continued.

I called Mollie, my youngest. Mollie has been learning ping pong for the past five years. She got really good really fast.

She beats me maybe 1/3 of the time. And crushes my friends.

“Guess what?” I said. … “What?”

“Everything I know about ping pong…Everything!…has been 100% wrong.”

“That’s horrible,” she said and she sounded disappointed. “That means everything I know has been wrong also. Because I learned everything from you!”

“No,” I said, “It’s ok. You’re already good enough to have fun and to play games with just about anyone.”

“But you just told me I’m doing everything wrong,” she said.

“Yeah,” I said, “Which means imagine how good you’re going to be once you start doing things right;.”

She grew up in an A+ / “Participation Trophy” culture. But real life is, at best, is a C-.

Heck, even adults now get the participation trophy.

If I break my Apple laptop, the simplest computer in the world to use, I go to the Apple store.

They don’t send me to the “Stupid line” to get my computer fixed. They send me to the “Genius Bar”.

So even at the Apple store I get a participation trophy. All I have to do is smash one of their computers. And I’ve smashed quite a few.

THE TAO OF NOTHING

The simple mantra, “I know nothing” has helped me so many times in the past seven years.

1) I always invest with a CEO and management team who have already succeeded in the exact industry they plan to succeed in again. They know MUCH MORE than me.2) I don’t invest until I know there are investors investing alongside of me who are much smarter than me. I know how smart investors research. They turn over every rock. I just want to piggyback on their work for free.

If someone is not honest, I can never trust what I am learning or how I can deliver value.

Which ultimately means I can’t trust that I will make money.

Hence: whether it’s a boss, a shareholder, a partner, a customer: one strike and you’re out. Even an employee (on integrity).

LEADERSHIP

1) I don’t want to talk to employees. If they work with me, then they know more than me about what they do.

I’m just there to provide intuition from experience. To show them when they don’t know something.

If I have to worry about something too much (talk to them too much) then they are not a good fit for their job.

Then I have to decide: do they love what they do? If yes, then find them a better fit for their skills. If no, then they will have a better time at another job.

2) Why?

The best way to motivate people is to share my sincere vision of why we are doing what we are doing. How are we helping people? Why I think the way I do.

Then I simply trust that they know more than me, their motivated to do what they do, and will come to me if they can’t do it anymore.

3) Call your mother!

Every day at my first job I was on such a steep learning curve I’d call my mother at the end of the day.

“Guess what I learned?” I said. “What?” “Guess!!” I was so excited.

I want every employee to call their mother at the end of a day (or partner, or friend, or whoever) and have that conversation.

Else, I’m not doing my job. Which is to work for the employees, who are smarter than me, so they can fulfill the vision for the customers.

What’s the goal?

Every employee should eventually leave and start a better competitor to me. Everyone should pass me. Else I’m not the stupidest person in the room.

I ran into one of my ex-employees from 20 years ago at Times Square.

He has his own company. He split off from mine and started his. I was happy for him.

He told me, 20 years later, “When I’m walking the office floor, I think of two people: my commander in the Israeli Army, and you.”

This is a humble brag. He made me really happy. I learned from him that I had done the right thing in pushing him to leave and start a competitor.

FRIENDSHIP

– This is what I learned from you.– This is what impresses me about what you are doing right now– What are your up to now?– WOW! (on the good stuff). LISTEN (on the bad stuff) RESPOND (on questions, with the qualification that I know nothing).– I’m going to throw my bad ideas at you.– I’m going to listen to what you have to say about my life.– Let’s have fun.

If I can’t do the above in most meetings with my friends, then I probably need new friends.

I learned so much from him I probably go back to that podcast (or post) and listen or re-read it at least once a month. Why not learn from the best negotiator ever?

But if you forget everything, there’s one mantra I say: “I know nothing”.

So…if selling a service for instance and asked “what price?”, if I forget all the cognitive biases on anchoring and recency and reciprocity, etc I have one go-to technique.

“You’re the expert at what you can pay. I feel like this is an amateur playing chess with a grandmaster. Give me advice on what you would do if you were me and wanted to provide the best possible service that would also create an ongoing relationship and make you look good to your bosses?”

That’s it. Get advice from the person you are negotiating with. If I’m the dumbest person around, and I trust them (see “RELATIONSHIPS”) then they will provide good advice even if they are on the opposite side of the table. This ALWAYS works.

ROMANTIC RELATIONSHIPS

I’m really an idiot here. I truly am the dumbest person in the room.

But if I always admit what I don’t know, what I’m not good at, what I’m afraid of…this is the base line self awareness to make a relationship work.

When I can’t admit what I don’t know, when I can’t admit what I’m afraid of, and I try to survive despite those things…then things go bad. Very bad.

DOING

I start off stupid.

I learn.

I do. The only way to get better is to DO. Not think or write or watch. DO.

This is the problem:

When I look up to everyone…when I’m always saying, “I know nothing”…then everyone seems so experienced and knowledgeable and sometimes even intimidating.

It’s exactly how I felt when I was ten years old.

Or when I was 24 and entering the workplace. Or when I was 27 and starting my first company.

It was exactly how I felt when I was young and excited and on the steepest learning curves.

That was then.

And now it’s now. No difference.

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